Would you rather be attacked by 1,000 wasps or 1 dog? A thousand paper cuts or one light stabbing? Global outages are bad but the choice isn’t global pain vs local pleasure. Local and global both bring pain, with different, complicated tradeoffs.
Cloudflare is down and hundreds of well paid engineers spring into action to resolve the issue. Your server goes down and you can’t get ahold of your Server Person because they’re at a cabin deep in the woods.
It's not "1,000 wasps or 1 dog", it's "1,000 dogs at once, or "1 dog at once, 1,000 different times". Rare but huge and coordinated siege, or a steady and predictable background radiation of small issues.
The latter is easier to handle, easier to fix, and much more suvivable if you do fuck it up a bit. It gives you some leeway to learn from mistakes.
If you make a mistake during the 1000 dog siege, or if you don't have enough guards on standby and ready to go just in case of this rare event, you're just cooked.
Cloudflare is down and hundreds of well paid engineers spring into action to resolve the issue. Your server goes down and you can’t get ahold of your Server Person because they’re at a cabin deep in the woods.